I would say an answer of "yes" is a huge red flag. A good CEO needs to understand risk/reward. VCs are investing in risky things, and thus distribute their cash

I would say an answer of "yes" is a huge red flag. A good CEO needs to understand risk/reward. VCs are investing in risky things, and thus distribute their cash amongst hundreds of start ups, fully aware that most will go to zero. It doesn't matter because 1 will go to $1 billion. OTOH, family usually can't afford to lose what they give. They make emotional decisions, not financially rational ones. If a CEO can't distinguish those entire distinguish those entirely different cases I doubt their financial acumen. You go to VC for moon shots, to the bank for proven business models, and to family and friends to build a family 'lifestyle' and asset heavy businesses (asset heavy so you can recoup some of the money if your business fails). No one rational should believe that their startup will succeed no matter what. We know, with certainty, that it almost certainly will fail. It's a flutter - a bet on a fabulous future (fabulous in terms of success, making a difference, huge wads of cash, whatever). If VCs expect that kind of naivety, well, you get what you pay for. How many other ways will that CEO be naive?